Triethylamine → HCID 67521562, compound

Participants

Reaction Conditions

Reaction Steps

N4-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)[1,5]naphthyridine-3,4-diamine (2.12 g, 6.67 mmol) was dissolved in 35 mL of anhydrous CH2Cl2 and the solution cooled to 0° C. and stirred under N2. Triethylamine (974 μL, 7.00 mmol) and ethoxyacetyl chloride (768 μL g, 7.00 mmol) were then added and the reaction mixture was stirred for 1 hour. The reaction mixture was then concentrated under reduced pressure to give a brown syrup. The brown syrup was dissolved in 50 mL of ethanol and treated with 4 mL of triethylamine. The mixture was heated to reflux for 3 days and then concentrated under reduced pressure. The resulting material was dissolved in 50 mL of CH2Cl2 and washed successively with H2O (2×50 mL) and brine (50 mL). The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 10-20% CMA/CHCl3), gave 2.30 g of 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridine as a purple solid.

Provenance & Evidence